Ternary herbicide combinations

ABSTRACT

Herbicide combinations comprising an effective amount of components (A), (B) and (C) wherein
     (A) denotes one or more herbicides selected from the group of compounds of the formula (I) and salts thereof   

     
       
         
         
             
             
         
       
         
         (B) denotes one or more herbicides selected from the group of the compounds of the formula (II) and their salts 
       
    
     
       
         
         
             
             
         
       
         
         (C) denotes at least one compound selected from the group consisting of
       (C-1) thienecarbazone-methyl;   (C-2) pyroxsulam;   (C-3) halauxifen;   (C-4) pinoxaden;   (C-5) pyroxasulfone;
           and/or salts thereof.

CROSS-REFERENCE TO RELATED APPLICATIONS

This is a Continuation Application of U.S. patent application Ser. No.14/910,516, filed Feb. 5, 2016, which is a § 371 National StageApplication of PCT/EP2014/066777, filed Aug. 5, 2014, which claimspriority to European Application No. 13179813.4, filed Aug. 9, 2013.Each of these applications is incorporated by reference in its entirety.

BACKGROUND OF THE INVENTION Field of the Invention Description

The invention is in the technical field of crop protection productswhich can be employed against harmful plants, for example in cropplants, and which comprise, as active compounds, a combination of atleast three herbicides.

Description of Related Art

The documents WO 92/13845 and WO 95/10507 disclose sulfonylureas andtheir salts and also their use as herbicides and/or plant growthregulators.

WO 03/073854 discloses ternary combinations containing the sulfonylureaherbicides iodosulfuron and mesosulfuron and further herbicides, such asprocarbazone.

WO 2004/080171 A2 discloses synergistic herbicidal mixtures comprisingA) pyroxsulam or its salts, B) at least one herbicidal compound selectedfrom a long list of further herbicides, and, if desired, C) at least onesafener.

U.S. Pat. No. 6,221,809 B1 discloses binary combinations comprising (i)mesosulfuron or a salt thereof, and (ii) a further herbicide, amongwhich iodosulfuron is mentioned.

U.S. Pat. No. 6,492,301 B1 and U.S. Pat. No. 6,864,217 B1 discloseherbicidal compositions containing (i) at least one herbicidally activecompound from the group of certain substituted phenylsulfonylureas andtheir agriculturally acceptable salts, and (ii) at least one compoundfrom the group of herbicides which are selective in rice.

WO 2009/029518 A2 discloses combinations containing (i) a pyridine orpyrimidine carboxylic acid component, such as for example halauxifen,and (ii) a second cereal or rice herbicide component, wherein inter aliasulfonylurea herbicides such as iodosulfuron and mesosulfuron arementioned.

WO 2011/107741 A1 discloses herbicidal compositions comprising a mixtureof (a) a first herbicide of a certain type and (b) pinoxaden.

Substituted thien-3-ylsulfonylamino(thio)carbonyltriazolin(ethi)ones areknown to be effective herbicides (cf. WO 01/05788).

The efficacy of these herbicides against harmful plants in the cropplants is at a high level, but depends in general on the applicationrate, the formulation in question, the harmful plants or spectrum ofharmful plants to be controlled in each case, the climatic conditions,the soil conditions and the like. Another criterion is the duration ofaction, or the breakdown rate of the herbicide. If appropriate, changesin the sensitivity of harmful plants, which may occur upon prolonged useof the herbicides or within geographic limitations must also be takeninto consideration. The compensation of losses in action in the case ofindividual harmful plants by increasing the application rates of theherbicides is only possible to a certain degree, for example becausesuch a procedure frequently reduces the selectivity of the herbicides orbecause the action is not improved, even when applying higher rates. Insome cases, the selectivity in crops can be improved by adding safeners.In general, however, there remains a need for methods to achieve theherbicidal action with a lower application rate of active compounds. Notonly does a lower application rate reduce the amount of an activecompound required for application, but, as a rule, it also reduces theamount of formulation auxiliaries required. It both reduces the economicinput and improves the ecological compatibility of the herbicidetreatment.

One possibility of improving the application profile of a herbicide canconsist in combining the active compound with one or more other activecompounds. However, the combined use of a plurality of active compoundsfrequently causes phenomena of physical and biological incompatibility,for example a lack of stability in a coformulation, decomposition of anactive compound, or antagonism of the active compounds. What is desiredare, in contrast, combinations of active compounds having anadvantageous activity profile, high stability and, if possible, asynergistically improved action, which allows the application rate to bereduced in comparison with the individual application of the activecompounds to be combined.

Surprisingly, it has now been found that

-   -   certain active compounds from the group of sulfonylureas or        their salts in combination with    -   certain herbicides, preferably ALS inhibiting herbicides from        the group of the sulfonylamino-carbonyltriazolinones, in        particular, thiencarbazone (C)        act together in a particularly advantageous manner, for example        when they are employed in crop plants which are suitable for the        selective use of the herbicides, if appropriate with addition of        safeners.

SUMMARY

The invention therefore provides herbicide combinations comprising aneffective amount of components (A), (B) and (C), wherein

-   (A) denotes one or more herbicides selected from the group of the    compounds of the formula (I) and their salts

-   -   wherein R is hydrogen or a C₁-C₅-alkyl group, preferably R is        methyl;

-   (B) denotes one or more herbicides selected from the group of the    compounds of the formula (II) and their salts

-   -   wherein R is hydrogen or a C₁-C₅-alkyl group, preferably R is        methyl;

-   (C) denotes at least one compound selected from the group consisting    of    -   (C-1) thienecarbazone-methyl;    -   (C-2) pyroxsulam;    -   (C-3) halauxifen;    -   (C-4) pinoxaden;    -   (C-5) pyroxasulfone;        -   and/or salts or esters thereof.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

If, in the context of this description, the short form of the commonname of an active compound is used, this includes in each case allcustomary derivatives, such as the esters and salts, and isomers, inparticular optical isomers, in particular the commercially availableform or forms. If the common name denotes an ester or salt, this in eachcase also comprises all other customary derivatives, such as otheresters and salts, the free acids and neutral compounds, and isomers, inparticular optical isomers, in particular the commercially availableform or forms. The given chemical compound names denote at least one ofthe compounds embraced by the common name, frequently a preferredcompound. In the case of sulfonamides such as sulfonylureas, salts alsoinclude the salts formed by exchanging a hydrogen atom on thesulfonamide group by a cation.

The herbicide (C) is suitable for controlling monocotyledonous anddicotyledonous harmful plants.

The salts of compounds of the formulae (I) and (II) in the context ofthe present invention preferably are in the form of the respectivealkali metal salts, alkaline earth salts or ammonium salts, preferablyin the form of the respective alkali metal salts, more preferably in theform of the respective sodium or potassium salts, most preferably in theform of the respective sodium salts.

The salts of compounds (C) in the context of the present inventionpreferably are in the form of the respective alkali metal salts,alkaline earth salts or ammonium salts, preferably in the form of therespective alkali metal salts, more preferably in the form of therespective sodium or potassium salts, most preferably in the form of therespective sodium salts.

The herbicide combinations according to the invention comprise aherbicidally effective amount of components (A), (B) and (C) and maycomprise further components, for example agrochemically active compoundsof a different type and/or formulation auxiliaries and/or additivescustomary in crop protection, or they may be employed together withthese. Preference is given to herbicide combinations comprising asynergistically effective amount of components (A), (B) and (C).

In a preferred embodiment, the herbicide combinations according to theinvention have synergistic effects. The synergistic effects areobserved, for example, when the active compounds (A), (B) and (C) areapplied together, but they can frequently also be observed when thecompounds are applied as a split application over time. Anotherpossibility is the application of the individual herbicides or theherbicide combinations in a plurality of portions (sequentialapplication), for example after pre-emergence applications, followed bypost-emergence applications or after early post-emergence applications,followed by applications at medium or late post-emergence.

Preferred is the simultaneous or nearly simultaneous application of theactive compounds of the herbicide combination according to theinvention. In a preferred embodiment, the herbicide combinationsaccording to the invention are mixtures or compositions comprising theactive compounds (A), (B) and (C) together.

The synergistic effects allow the application rates of the individualactive compounds to be reduced, a more potent action at the sameapplication rate, the control of hitherto uncontrollable species(activity gaps), an extended application period and/or a reduced numberof individual applications required and—as a result for the user—moreadvantageous weed control systems both from an economical and ecologicalpoint of view.

The above mentioned formulae (I) and (II) include all stereoisomers andtheir mixtures, in particular also racemic mixtures and—if enantiomersare possible—the respective biologically active enantiomer. Compounds ofthe formulae (I) and (II) and their salts and also their preparation aredescribed, for example, in WO 92/13845 and WO 95/10507. Preferredcompounds of the formulae (I) and their salts are methyl2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-4-methanesulfone-aminomethyl-benzoate(mesosulfuron-methyl, A1-1) and its salts, such as the sodium salt(mesosulfuron-methyl-sodium, A1-2) (see, for example, WO 95/10507 andAgrow No. 347, Mar. 3, 2000, page 22 (PJB Publications Ltd. 2000).Preferred compounds of the formula (II) and their salts are3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-1-(2-methoxycarbonyl-5-iodophenyl-sulfonyl)urea(iodosulfuron-methyl, B1-1) and its salts, such as the sodium saltidodosulfuron-methyl-sodium, B1-2) (see, for example, WO 92/13845 andPM, pp. 547-548).

Preferred (C) compounds are selected from

-   (C-1) methyl    4-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonylsulfamoyl]-5-methylthiophene-3-carboxylate,    having the ISO name thienecarbazone-methyl (CAS No. 317815-83-1),    (C1-1) described in WO 01/05788.

-   -   and its salts, preferably its sodium salt (C1-2);

-   (C-2)    N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)-3-pyridinesulfonamide,    having the ISO name pyroxsulam (CAS no. 422556-08-9) (C2-1) and its    salts or esters;

-   (C-3)    4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic    acid, having the ISO name halauxifen (CAS no. 943832-60-8) (C3-1)    and its salts or esters, preferably halauxifen-methyl ester (CAS no.    943831-98-9) (C3-2).

-   (C-4)    8-(2,6-diethyl-4-methylphenyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin-9-yl    2,2-dimethylpropanoate having the ISO name pinoxaden (CAS no.    243973-20-8) (C4-1) and its salts or esters;

-   (C-5)    3-[[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole    having the ISO name pyroxasulfone (CAS no. 447399-55-5) (C5-1) and    its salts or esters;

The abovementioned active compounds (A) and (B) and their salts arecapable of inhibiting the enzyme acetolactate synthase (ALS) and thusprotein synthesis in plants. The application rate of the activecompounds of the formulae (A), (B) and (C) and/or their salts can bevaried within a wide range, for example between 0.001 and 0.5 kg ofAS/ha, preferably 0.010 and 0.100 kg of AS/ha, most preferably 0.035 to0.05. kgAS/ha. The abbreviation AS/ha used in this description means“active substance per hectare”, based on 100% active compound. In thecase of applications at application rates of 0.01 to 0.2 kg of AS/ha ofthe active compounds (A) and (B) and their salts, preferably the activecompounds (A1-1), (A1-2), (B1-1) and (B1-2), a relatively broad spectrumof annual and perennial broad-leaved weeds, weed grasses and Cyperaceais controlled pre- and post-emergence. In the combinations according tothe invention, the application rates are generally lower, for example inthe range from 0.1 to 100 g of AS/ha, preferably from 0.5 to 50 g ofAS/ha.

In a preferred embodiment of the invention

-   (C-1) thienecarbazone-methyl and/or its salts is applied at a rate    of 0.005 to 0.020 kg of AS/ha, preferably 0.007 to 0.015 kg of    AS/ha, most preferably 0.0075 to 0.010 kg of AS/ha;-   (C-2) pyroxsulam and/or its salts or esters is applied at a rate of    0.005 to 0.050 kg of AS/ha, preferably 0.010 to 0.025 kg of AS/ha,    most preferably 0.018 to 0.020 kg of AS/ha;-   (C-3) halauxifen and/or its salts or esters is applied at a rate of    0.005 to 0.020 kg of AS/ha, preferably 0.005 to 0.015 kg of AS/ha,    most preferably 0.008 to 0.010 kg of AS/ha;-   (C-4) pinoxaden and/or its salts or esters is applied at a rate of    0.005 to 0.100 kg of AS/ha, preferably 0.050 to 0.080 kg of AS/ha,    most preferably 0.060 to 0.065 kg of AS/ha;-   (C-5) pyroxasulfone and/or its salts or esters is applied at a rate    of 0.050 to 0.500 kg of AS/ha, preferably 0.080 to 0.250 kg of    AS/ha, most preferably 0.100 to 0.150 kg of AS/ha.

The active compounds can generally be formulated as water-solublewettable powders (WP), water-dispersible granules (WDG),water-emulsifiable granules (WEG), suspoemulsion (SE), oil suspensionconcentrate (SC) or oil dispersion (OD).

The weight ratio of the components A and B to one another is between10:1 to 1:10 preferably 8:1 to 1:2, most preferably 5:1 to 1:1.

The ratios of the application rates (A+B):C which are generally used arestated hereinabove and identify the weight ratio of the two components(A+B) and C to each other is generally 5:1 to 1:5, preferably 4:1 to1:2, and most preferably 1.5:1 to 1:1.

The preferred weight ratio of the two components (A+B) and (C-1) to eachother is advantageously 5:1 to 1:3, preferably 4:1 to 1:2, morepreferably 3:1 to 1:1, and most preferably 5:2 to 3:2.

The preferred weight ratio of the two components (A+B) and (C-2) to eachother is advantageously 3:1 to 1:4, preferably 2:1 to 1:3, morepreferably 3:2 to 2:5, and most preferably 1:1 to 1:2.

The preferred weight ratio of the two components (A+B) and (C-4) to eachother is advantageously 2:1 to 1:5, preferably 3:2 to 1:5, morepreferably 1:1 to 1:4, and most preferably 1:2 to 1:4.

For use of the active compounds of the formulae (I) and (II) or theirsalts in plant crops, it is expedient, depending on the plant crop, toapply a safener from certain application rates upward in order to reduceor to avoid possible damage to the crop plants. Examples of suitablesafeners are those which have a safener action in combination withsulfonylurea herbicides, preferably phenylsulfonylureas. Suitablesafeners are disclosed in WO-A-96/14747 and the literature citedtherein.

The following groups of compounds are examples of suitable safeners forthe abovementioned herbicidally active compounds (A) and (B):

-   a) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid (S1)    type, preferably compounds such as ethyl    1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate    (S1-1, mefenpyr-diethyl, PM, pp. 594-595), and related compounds as    they are described for example in WO 91/07874 and PM (pp. 594-595).-   b) Dichlorophenylpyrazolecarboxylic acid derivatives, preferably    compounds such as ethyl    1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl    1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3),    ethyl    1-(2,4-dichlorophenyl)-5-(1,1-dimethyl-ethyl)pyrazole-3-carboxylate    (S1-4), ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate    (S1-5) and related compounds as are described in EP-A-333 131 and    EP-A-269 806.-   c) Compounds of the triazolecarboxylic acid (S1) type, preferably    compounds such as fenchlorazole, i.e. ethyl    1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate    (S1-6) and related compounds (see EP-A-174 562 and EP-A-346 620).-   d) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic    acid type or of the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid    type, preferably compounds such as ethyl    5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-7) or ethyl    5-phenyl-2-isoxazoline-3-carboxylate (S1-8) and related compounds as    are described in WO 91/08202, or of ethyl    5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-9, isoxadifen-ethyl) or    n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-10) or ethyl    5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (51-11), as    are described in patent application (WO-A-95/07897).-   e) Compounds of the 8-quinoline oxyacetic acid (S2) type, preferably-   1-methylhex-1-yl (5-chloro-8-quinolinoxy)acetate (S2-1,    cloquintocet-mexyl, e.g. PM (pp. 195-196),-   (1,3-dimethylbut-1-yl) (5-chloro-8-quinolinoxy)acetate (S2-2),-   4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3),-   1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4),-   ethyl (5-chloro-8-quinolinoxy)acetate (S2-5),-   methyl (5-chloro-8-quinolinoxy)acetate (S2-6),-   allyl (5-chloro-8-quinolinoxy)acetate (S2-7),-   2-(2-propylideneiminooxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate    (S2-8),-   2-oxoprop-1-yl (5-chloro-8-quinolinoxy)acetate (S2-9)-   and related compounds as are described in EP-A-86 750, EP-A-94 349    and EP-A-191 736 or EP-A-0 492 366.-   f) Compounds of the (5-chloro-8-quinolinoxy)malonic acid type,    preferably compounds such as diethyl    (5-chloro-8-quinolinoxy)malonate, diallyl    (5-chloro-8-quinolinoxy)malonate, methyl ethyl    (5-chloro-8-quinolinoxy)-malonate and related compounds as are    described in EP-A-0 582 198.-   g) Active compounds of the phenoxyacetic acids, phenoxypropionic    acids or aromatic carboxylic acids type, such as, for example,    2,4-dichlorophenoxyacetic acid (and esters) (2,4-D),    4-chloro-2-methylphenoxypropionic esters (mecoprop), MCPA or    3,6-dichloro-2-methoxybenzoic acid (and esters) (dicamba).

In many cases, the abovementioned safeners are also suitable for activecompounds of group (C). In addition, the following safeners are suitablefor the herbicide combinations according to the invention:

-   h) active compounds of the pyrimidine type, such as, for example,    “fenclorim” (PM, pp. 386-387) (=4,6-dichloro-2-phenylpyrimidine),-   i) active compounds of the dichloroacetamide type, which are    frequently used as pre-emergence safeners (soil-acting safeners)    such as, for example,-   “dichloromid” (PM, pp. 270-271)    (═N,N-diallyl-2,2-dichloroacetamide),-   “AR-29148” (=3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidone by    Stauffer),-   “benoxacor” (PM, pp. 74-75)    (=4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine),-   “APPG-1292” (═N-allyl-N[(1,3-dioxolan-2-yl)-methyl]dichloroacetamide    by PPG Industries),-   “ADK-24” (═N-allyl-N-[(allylaminocarbonyl)-methyl]-dichloroacetamide    by Sagro-Chem),-   “AAD-67” or “AMON 4660”    (=3-dichloroacetyl-1-oxa-3-aza-spiro[4,5]decane by Nitrokemia or    Monsanto),-   “diclonon” or “ABAS145138” or “ALAB145138”    (=(=3-dichloroacetyl-2,5,5-trimethyl-1,3-diazabicyclo[4.3.0]nonane    by BASF) and-   “furilazol” or “AMON 13900” (see PM, 482-483)    (═(RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidone)-   j) active compounds of the dichloroacetone derivatives type, such    as, for example,-   “AMG 191” (CAS Reg. No. 96420-72-3)    (=2-dichloromethyl-2-methyl-1,3-dioxolane by Nitrokemia),-   k) active compounds of the oxyimino compounds type which are known    as seed-dressing materials such as, for example,-   “oxabetrinil” (PM, p. 689)    (═(Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile), which is    known as safener in seed dressing to prevent metolachlor damage,-   “fluxofenim” (PM, pp. 467-468)    (=1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone    O-(1,3-dioxolan-2-ylmethyl)-oxime, which is known as safener in seed    dressing to prevent metolachlor damage, and-   “cyometrinil” or “A-CGA-43089” (PM, p. 983)    (═(Z)-cyanomethoxyimino(phenyl)acetonitrile), which is known as    safener in seed dressing to prevent metolachlor damage,-   l) active compounds of the thiazolecarboxylic esters type, which are    known as seed-dressing materials, such as, for example,    -   “flurazol” (PM, pp. 450-451) (=benzyl        2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate), which is        known as safener in seed dressing to prevent alachlor and        metolachlor damage,-   m) active compounds of the naphthalenedicarboxylic acid derivatives    type which are known as seed-dressing agents, such as, for example,-   “naphthalic anhydride” (PM, pp. 1009-1010)    (=1,8-naphthalenedicarboxylic anhydride), which is known as safener    for maize in seed dressing to prevent thiocarbamate herbicide    damage,-   n) active compounds of the chromaneacetic acid derivatives type,    such as, for example,-   “ACL 304415” (CAS Reg. No. 31541-57-8)    (=2-84-carboxychroman-4-yl)acetic acid by American Cyanamid),-   o) active compounds which, in addition to a herbicidal action    against harmful plants, also have a safener action on crop plants,    such as, for example,-   “dimepiperate” or “AMY-93” (PM, pp. 302-303)    (═S-1-methyl-1-phenylethyl piperidine-1-carbothioate),-   “daimuron” or “ASK 23” (PM, p. 247)    (=1-(1-methyl-1-phenylethyl)-3-p-tolylurea),-   “cumyluron”=“AJC-940”    (=3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenyl-ethyl)urea, see    JP-A-60087254),-   “methoxyphenon” or “ANK 049”    (=3,3′-dimethyl-4-methoxy-benzophenone),-   “CSB” (=1-bromo-4-(chloromethylsulfonyl)benzene) (CAS Reg. No.    54091-06-4 by Kumiai).

The herbicides (A) and (B), if appropriate in the presence of safeners(the combination (A1-2)+(S1-1), for example, is commercially availableas Sigma® OD, and the combination (A1-2)+(B1-2)+(S1-1) as Atlantis® WG),are suitable for controlling harmful plants in plant crops, for examplein economically important crops such as cereals (such as wheat, barley,rye, oats, rice, corn, millet), sugar beet, sugar cane, oilseed rape,cotton and soybeans. Of particular interest is the application inmonocotyledonous crops such as cereals, for example wheat, barley, rye,oats, in particular hybrids thereof such as triticale, rice, corn andmillet. These crops are also preferred for the combinations (A)+(B)+(C).

Also included according to the invention are those herbicidecombinations which, in addition to components (A), (B) and (C), alsocomprise one or more further agrochemically active compounds of adifferent structure, such as herbicides, insecticides, fungicides orsafeners. To such combinations, the preferred conditions illustratedbelow in particular for combinations (A)+(B)+(C) according to theinvention also primarily apply, if they comprise the combinations(A)+(B)+(C) according to the invention, and with respect to thecombination (A)+(B)+(C) in question.

Of particular interest are herbicidal compositions according to thepresent invention and the use of herbicidal compositions according tothe present invention comprising the following compounds (A)+(B)+(C),preferably mixtures or compositions comprising the active compounds (A),(B) and (C) together:(A1-1)+(B1-1)+(C1-1),(A1-2)+(B1-1)+(C1-1);(A1-1)+(B1-2)+(C1-1);(A1-2)+(B1-2)+(C1-1);(A1-1)+(B1-1)+(C1-2),(A1-2)+(B1-1)+(C1-2);(A1-1)+(B1-2)+(C1-2);(A1-2)+(B1-2)+(C1-2);(A1-1)+(B1-1)+(C2-1),(A1-2)+(B1-1)+(C2-1);(A1-1)+(B1-2)+(C2-1);(A1-2)+(B1-2)+(C2-1);(A1-1)+(B1-1)+(C3-1),(A1-2)+(B1-1)+(C3-1);(A1-1)+(B1-2)+(C3-1);(A1-2)+(B1-2)+(C3-1);(A1-1)+(B1-1)+(C3-2),(A1-2)+(B1-1)+(C3-2);(A1-1)+(B1-2)+(C3-2);(A1-2)+(B1-2)+(C3-2);(A1-1)+(B1-1)+(C4-1),(A1-2)+(B1-1)+(C4-1);(A1-1)+(B1-2)+(C4-1);(A1-2)+(B1-2)+(C4-1);(A1-1)+(B1-1)+(C5-1),(A1-2)+(B1-1)+(C5-1);(A1-1)+(B1-2)+(C5-1);(A1-2)+(B1-2)+(C5-1).

In addition, each of the herbicide combinations mentioned above(preferably the mixtures or compositions comprising the active compounds(A), (B) and (C) together) may additionally comprise one or moresafeners, in particular a safener such as mefenpyr-diethyl (S1-1),isoxadifen-ethyl (S1-9) and cloquintocet-mexyl (S2-1). Preference is ineach case given to the ranges of application rates and ratios ofapplication rates mentioned above. Examples of this are the herbicidecombinations listed below.(A1-1)+(B1-1)+(C1-1)+(S1-1),(A1-2)+(B1-1)+(C1-1)+(S1-1);(A1-1)+(B1-2)+(C1-1)+(S1-1);(A1-2)+(B1-2)+(C1-1)+(S1-1);(A1-1)+(B1-1)+(C1-2)+(S1-1),(A1-2)+(B1-1)+(C1-2)+(S1-1);(A1-1)+(B1-2)+(C1-2)+(S1-1);(A1-2)+(B1-2)+(C1-2)+(S1-1);(A1-1)+(B1-1)+(C2-1)+(S1-1),(A1-2)+(B1-1)+(C2-1)+(S1-1);(A1-1)+(B1-2)+(C2-1)+(S1-1);(A1-2)+(B1-2)+(C2-1)+(S1-1);(A1-1)+(B1-1)+(C3-1)+(S1-1),(A1-2)+(B1-1)+(C3-1)+(S1-1);(A1-1)+(B1-2)+(C3-1)+(S1-1);(A1-2)+(B1-2)+(C3-1)+(S1-1);(A1-1)+(B1-1)+(C3-2)+(S1-1),(A1-2)+(B1-1)+(C3-2)+(S1-1);(A1-1)+(B1-2)+(C3-2)+(S1-1);(A1-2)+(B1-2)+(C3-2)+(S1-1);(A1-1)+(B1-1)+(C4-1)+(S1-1),(A1-2)+(B1-1)+(C4-1)+(S1-1);(A1-1)+(B1-2)+(C4-1)+(S1-1);(A1-2)+(B1-2)+(C4-1)+(S1-1);(A1-1)+(B1-1)+(C5-1)+(S1-1),(A1-2)+(B1-1)+(C5-1)+(S1-1);(A1-1)+(B1-2)+(C5-1)+(S1-1);(A1-2)+(B1-2)+(C5-1)+(S1-1);(A1-1)+(B1-1)+(C1-1)+(S1-9),(A1-2)+(B1-1)+(C1-1)+(S1-9);(A1-1)+(B1-2)+(C1-1)+(S1-9);(A1-2)+(B1-2)+(C1-1)+(S1-9);(A1-1)+(B1-1)+(C1-2)+(S1-9);(A1-2)+(B1-1)+(C1-2)+(S1-9);(A1-1)+(B1-2)+(C1-2)+(S1-9);(A1-2)+(B1-2)+(C1-2)+(S1-9);(A1-1)+(B1-1)+(C2-1)+(S1-9);(A1-2)+(B1-1)+(C2-1)+(S1-9);(A1-1)+(B1-2)+(C2-1)+(S1-9);(A1-2)+(B1-2)+(C2-1)+(S1-9);(A1-1)+(B1-1)+(C3-1)+(S1-9);(A1-2)+(B1-1)+(C3-1)+(S1-9);(A1-1)+(B1-2)+(C3-1)+(S1-9);(A1-2)+(B1-2)+(C3-1)+(S1-9);(A1-1)+(B1-1)+(C3-2)+(S1-9);(A1-2)+(B1-1)+(C3-2)+(S1-9);(A1-1)+(B1-2)+(C3-2)+(S1-9);(A1-2)+(B1-2)+(C3-2)+(S1-9);(A1-1)+(B1-1)+(C4-1)+(S1-9);(A1-2)+(B1-1)+(C4-1)+(S1-9);(A1-1)+(B1-2)+(C4-1)+(S1-9);(A1-2)+(B1-2)+(C4-1)+(S1-9);(A1-1)+(B1-1)+(C5-1)+(S1-9);(A1-2)+(B1-1)+(C5-1)+(S1-9);(A1-1)+(B1-2)+(C5-1)+(S1-9);(A1-2)+(B1-2)+(C5-1)+(S1-9);(A1-1)+(B1-1)+(C1-1)+(S2-1);(A1-2)+(B1-1)+(C1-1)+(S2-1);(A1-1)+(B1-2)+(C1-1)+(S2-1);(A1-2)+(B1-2)+(C1-1)+(S2-1);(A1-1)+(B1-1)+(C1-2)+(S2-1);(A1-2)+(B1-1)+(C1-2)+(S2-1);(A1-1)+(B1-2)+(C1-2)+(S2-1);(A1-2)+(B1-2)+(C1-2)+(S2-1);(A1-1)+(B1-1)+(C2-1)+(S2-1);(A1-2)+(B1-1)+(C2-1)+(S2-1);(A1-1)+(B1-2)+(C2-1)+(S2-1);(A1-2)+(B1-2)+(C2-1)+(S2-1);(A1-1)+(B1-1)+(C3-1)+(S2-1);(A1-2)+(B1-1)+(C3-1)+(S2-1);(A1-1)+(B1-2)+(C3-1)+(S2-1);(A1-2)+(B1-2)+(C3-1)+(S2-1);(A1-1)+(B1-1)+(C3-2)+(S2-1);(A1-2)+(B1-1)+(C3-2)+(S2-1);(A1-1)+(B1-2)+(C3-2)+(S2-1);(A1-2)+(B1-2)+(C3-2)+(S2-1);(A1-1)+(B1-1)+(C4-1)+(S2-1);(A1-2)+(B1-1)+(C4-1)+(S2-1);(A1-1)+(B1-2)+(C4-1)+(S2-1);(A1-2)+(B1-2)+(C4-1)+(S2-1);(A1-1)+(B1-1)+(C5-1)+(S2-1);(A1-2)+(B1-1)+(C5-1)+(S2-1);(A1-1)+(B1-2)+(C5-1)+(S2-1);(A1-2)+(B1-2)+(C5-1)+(S2-1).

It may be advantageous to combine one or more herbicides (A) with one ormore herbicides (B) and one or more herbicides (C), for example aherbicide (A) with a herbicide (B) and one or more herbicides (C).Herbicide combinations according to the invention with a plurality ofherbicide C) are, for example, those which comprise, as component C),the following herbicide combinations: C1+C2, which preferably comprise,as components (A) and (B), the compounds (A1-1)+(B1-1), (A1-1)+(B1-2),(A1-2)+(B1-1) or (A1-2)+(B1-2), in particular (A1-1)+(B1-2), and whichmay additionally comprise a safener, such as (S1-1), (S1-9) or (S2-1),in particular (S1-1). Furthermore, the combinations of herbicidesaccording to the invention can be used together with otheragrochemically active compounds, for example from the group of thesafeners, fungicides, herbicides, insecticides and plant growthregulators, or with formulation auxiliaries and additives customary incrop protection. Additives are, for example, fertilizers and colorants.Preference is in each case given to the ratios of application rates andranges of application rates mentioned above.

The combinations according to the invention (=herbicidal compositions)have an outstanding herbicidal activity against a broad spectrum ofeconomically important monocotyledonous and dicotyledonous harmfulplants. The active compounds also act efficiently on perennial weedswhich produce shoots from rhizomes, rootstocks or other perennial organsand which are difficult to control. In this context, it does not matterwhether the substances are applied before sowing, pre-emergence orpost-emergence. Post-emergence application, or early post-sowingpre-emergence application, is preferred.

Specifically, examples may be mentioned of some representatives of themonocotyledonous and dicotyledonous weed flora which can be controlledby the combinations according to the invention, without the enumerationbeing a restriction to certain species.

Examples of weed species on which the herbicidal compositions actefficiently are, from amongst the monocotyledonous weed species, forexample Apera spica venti, Avena spp., Alopecurus spp., Brachiaria spp.,Digitaria spp., Lolium spp., Equinochloa spp., Panicum spp., Phalarisspp., Poa spp., Setaria spp. and also Bromus spp., such as Bromuscatharticus, Bromus secalinus, Bromus erectus, Bromus tectorum andBromus japonicus, and Cyperus species from the annual group, and,amongst the perennial species, Agropyron, Cynodon, Imperata and Sorghumand also perennial Cyperus species.

In the case of the dicotyledonous weed species, the spectrum of actionextends to species such as, for example, Abutilon spp., Amaranthus spp.,Chenopodium spp., Chrysanthemum spp., Galium spp. such as Galiumaparine, Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp.,Pharbitis spp., Polygonum spp., Sida spp., Sinapis spp., Solanum spp.,Stellaria spp., Veronica spp. and Viola spp., Xanthium spp., amongst theannuals, and Convolvulus, Cirsium, Rumex and Artemisia in the case ofthe perennial weeds.

If the herbicide combinations according to the invention are applied tothe soil surface before germination, then the weed seedlings are eitherprevented completely from emerging, or the weeds grow until they havereached the cotyledon stage but then their growth stops, and,eventually, after three to four weeks have elapsed, they die completely.

If the active compounds are applied post-emergence to the green parts ofthe plants, growth likewise stops drastically a very short time afterthe treatment and the weed plants remain at the growth stage of thepoint of time of application, or they die completely after a certaintime, so that in this manner competition by the weeds, which is harmfulto the crop plants, is eliminated at a very early point in time and in asustained manner.

The herbicidal compositions according to the invention are distinguishedby a rapidly commencing and long-lasting herbicidal action. As a rule,the rainfastness of the active compounds in the combinations accordingto the invention is advantageous. A particular advantage is that thedosages of the compounds (A), (B) and (C), which are used in thecombinations and are effective, can be adjusted to such a low quantitythat their soil action is optimally low. Not only does this allow themto be employed in sensitive crops in the first place, but groundwaterand surface water contaminations are virtually avoided. Theactive-ingredient combination according to the invention allows theapplication rate of the active compounds required to be reducedconsiderably.

In a preferred embodiment, when herbicides of the type (A)+(B)+(C) areused jointly, superadditive (=synergistic) effects are observed. Thismeans that the effect in the combinations exceeds the expected total ofthe effects of the individual herbicides employed. The synergisticeffects allow the application rate to be reduced, a broader spectrum ofbroad-leaved weeds and grass weeds to be controlled, the herbicidalaction to take place more rapidly, the duration of action to be longer,the harmful plants to be controlled better while using only one, or few,applications, and the application period which is possible to beextended. In some cases, the use of the compositions also reduces theamount of harmful ingredients, such as nitrogen or oleic acid, and theirintroduction into the soil.

The abovementioned properties and advantages are of benefit for weedcontrol practice to keep agricultural crops free from undesiredcompeting plants and thus to safeguard and/or increase the yields fromthe qualitative and quantitative point of view. These novel combinationsmarkedly exceed the technical state of the art with a view to theproperties described.

While the combinations according to the invention have an outstandingherbicidal activity against monocotyledonous and dicotyledonous weeds,the crop plants are damaged only to a minor extent, if at all.

Moreover, some of the compositions according to the invention haveoutstanding growth-regulatory properties on the crop plants. They engagein the plants' metabolism in a regulatory manner and can thus beemployed for provoking directed effects on plant constituents and tofacilitate harvesting such as for example by triggering desiccation andstunted growth. Moreover, they are also suitable for the general controland inhibition of undesired vegetative growth without simultaneouslydestroying the plants. An inhibition of vegetative growth is veryimportant in a large number of monocotyledonous and dicotyledonous cropssince yield losses as a result of lodging can thus be reduced, orprevented completely.

Owing to their herbicidal and plant-growth-regulatory properties, thecompositions according to the invention can be employed for controllingharmful plants in genetically modified crop plants or crop plantsobtained by mutation/selection. These crop plants are distinguished as arule by particular, advantageous properties, such as resistances toherbicidal compositions or resistances to plant diseases or causativeagents of plant diseases such as particular insects or microorganismssuch as fungi, bacteria or viruses. Other particular properties relate,for example, to the harvested material with regard to quantity, quality,storability, composition and specific constituents. Thus, for example,transgenic plants are known whose starch content is increased or whosestarch quality is altered, or those where the harvested material has adifferent fatty acid composition.

Conventional methods of generating novel plants which have modifiedproperties in comparison to plants occurring to date consist, forexample, in traditional breeding methods and the generation of mutants(see, for example, U.S. Pat. Nos. 5,162,602; 4,761,373; 4,443,971).Alternatively, novel plants with altered properties can be generatedwith the aid of recombinant methods (see, for example, EP-A-0221044,EP-A-0131624). For example, the following have been described in severalcases:

-   -   the modification, by recombinant technology, of crop plants with        the aim of modifying the starch synthesized in the plants (for        example WO 92/11376, WO 92/14827, WO 91/19806),    -   transgenic crop plants which exhibit resistances to other        herbicides, for example to sulfonylureas (EP-A-0257993, U.S.        Pat. No. 5,013,659),    -   transgenic crop plants with the capability of producing Bacillus        thuringiensis toxins (Bt toxins), which make the plants        resistant to certain pests (EP-A-0142924, EP-A-0193259),    -   transgenic crop plants with a modified fatty acid composition        (WO 91/13972).

A large number of techniques in molecular biology are known in principlewith the aid of which novel transgenic plants with modified propertiescan be generated: see, for example, Sambrook et al., 1989, MolecularCloning, A Laboratory Manual, 2^(nd) Edition, Cold Spring HarborLaboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene andKlone”, VCH Weinheim 2^(nd) Edition 1996 or Christou, “Trends in PlantScience” 1 (1996) 423-431).

To carry out such recombinant manipulations, nucleic acid moleculeswhich allow mutagenesis or sequence changes by recombination of DNAsequences can be introduced into plasmids. For example, theabovementioned standard methods allow base exchanges to be carried out,subsequences to be removed, or natural or synthetic sequences to beadded. To connect the DNA fragments to each other, adapters or linkersmay be added to the fragments.

For example, the generation of plant cells with a reduced activity of agene product can be achieved by expressing at least one correspondingantisense RNA, a sense RNA for achieving a cosuppression effect or byexpressing at least one suitably constructed ribosome which specificallycleaves transcripts of the abovementioned gene product.

To this end, it is possible to use DNA molecules which encompass theentire coding sequence of a gene product inclusive of any flankingsequences which may be present, and also DNA molecules which onlyencompass portions of the coding sequence, it being necessary for theseportions to be long enough to have an antisense effect in the cells. Theuse of DNA sequences which have a high degree of homology to theencoding sequences of a gene product, but are not completely identicalto them, is also possible.

When expressing nucleic acid molecules in plants, the proteinsynthesized can be localized in any desired compartment of the plantcell. However, to achieve localization in a particular compartment, itis possible, for example, to link the coding region with DNA sequenceswhich ensure localization in a particular compartment. Such sequencesare known to those skilled in the art (see, for example, Braun et al.,EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

The transgenic plant cells can be regenerated by known techniques togive rise to intact plants. In principle, the transgenic plants can beplants of any desired plant species, i.e. not only monocotyledonous, butalso dicotyledonous, plants. Thus, transgenic plants can be obtainedwhose properties are altered by overexpression, suppression orinhibition of homologous (=natural) genes or gene sequences or theexpression of heterologous (=foreign) genes or gene sequences.

The invention therefore also relates to a method of controllingundesired vegetation (e.g. harmful plants), preferably in plant cropssuch as cereals (e.g. wheat, barley, rye, oats, hybrids thereof such astriticale, rice, corn, millet), sugar beet, sugar cane, oilseed rape,cotton and soybeans, especially preferably in monocotyledonous cropssuch as cereals, for example wheat, barley, rye, oats, hybrids thereofsuch as triticale, rice, corn and millet, which comprises applying oneor more herbicides of type (A) together with one or more herbicides oftype (B) and one or more herbicides of type (C) jointly or separately,for example by the pre-emergence method, by the post-emergence method orby the pre-emergence and the post-emergence method, to the plants, forexample harmful plants, parts of these plants, plant seeds or the areawhere the plants grow, for example the area under cultivation.

The plant crops can also have been genetically modified or been obtainedby mutation selection and are preferably tolerant to acetolactatesynthase (ALS) inhibitors.

The invention also relates to the use of the novel combinations ofcompounds (A)+(B)+(C) for controlling harmful plants, preferably inplant crops.

The herbicidal compositions according to the invention can also be usednon-selectively for controlling unwanted vegetation, for example inplantation crops, in the borders of paths, in squares, in industrialplants or in railroad installations.

The active compound combinations according to the invention can existnot only as mixed formulations of the components (A), (B) and (C), ifappropriate together with further agrochemically active compounds,additives and/or customary formulation auxiliaries, which are thenapplied in the customary manner as a dilution with water, but also asso-called tank mixes by jointly diluting the separately formulated, orpartially separately formulated, components with water.

The compounds (A), (B) and (C) or their combinations can be formulatedin various ways, depending on the prevailing biological and/orchemical-physical parameters. The following are examples of generalpossibilities for formulations: wettable powders (WP), water-solubleconcentrates, emulsifiable concentrates (EC), aqueous solutions (SL),emulsions (EW) such as oil-in-water and water-in-oil emulsions,sprayable solutions or emulsions, suspension concentrates (SC), oildispersions (OD), oil- or water-based dispersions, suspoemulsions, dusts(DP), seed-dressing materials, granules for soil application or forbroadcasting, or water-dispersible granules (WG), ULV formulations,microcapsules or waxes.

The individual formulation types are known in principle and aredescribed for example, in: Winnacker-Küchler, “Chemische Technologic”,Volume 7, C. Hauser Verlag Munich, 4^(th) Edition, 1986; van Valkenburg,“Pesticide Formulations”, Marcel Dekker N.Y., 1973; K. Martens, “SprayDrying Handbook”, 3rd Ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required, such as inert materials,surfactants, solvents and other additives are also known and aredescribed, for example, in Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J.; H.v.Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley &Sons, N.Y. Marsden, “Solvents Guide”, 2nd Ed., Interscience, N.Y. 1950;McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Surface-active ethylene oxideadducts], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Küchler,“Chemische Technologic”, Volume 7, C. Hauser Verlag Munich, 4^(th)Edition 1986.

Based on these formulations, combinations with other agrochemicallyactive substances, such as other herbicides, fungicides or insecticides,and with safeners, fertilizers and/or growth regulators, may also beprepared, for example in the form of a readymix or a tank mix.

Wettable powders (sprayable powders) are products which are uniformlydispersible in water and which, besides the active compound, alsocomprise ionic or nonionic surfactants (wetters, dispersants), forexample polyoxethylated alkylphenols, polyethoxylated fatty alcohols orfatty amines, alkanesulfonates or alkylbenzenesulfonates, sodiumlignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate or else sodium oleoylmethyltauride, inaddition to a diluent or inert material.

Emulsifiable concentrates are prepared by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene or else higher-boiling aromatics orhydrocarbons with addition of one or more ionic or nonionic surfactants(emulsifiers). Examples of emulsifiers which may be used are: calciumsalts of alkylarylsulfonic acids, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters,alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propyleneoxide/ethylene oxide condensates, alkyl polyethers, sorbitan fatty acidesters, polyoxyethylene sorbitan fatty acid esters or polyoxethylenesorbitol esters.

Dusts are obtained by grinding the active compound with finely dividedsolid materials, for example talc, natural clays such as kaolin,bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates (SC) can be water- or oil-based. They can beprepared, for example, by wet grinding by means of commerciallyavailable bead mills and, if appropriate, addition of furthersurfactants as they have already been mentioned for example above in thecase of the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared forexample by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and, if appropriate, further surfactants ashave already been mentioned for example above in the case of the otherformulation types.

Granules can be prepared either by spraying the active compound ontoadsorptive, granulated inert material or by applying active compoundconcentrates to the surface of carriers such as sand, kaolinites orgranulated inert material with the aid of binders, for example polyvinylalcohol, sodium polyacrylate or else mineral oils. Suitable activecompounds may also be granulated in the manner conventionally used forthe production of fertilizer granules, if desired in a mixture withfertilizers. As a rule, water-dispersible granules are prepared bycustomary processes such as spray drying, fluidized-bed granulation,disk granulation, mixing with high-speed mixers and extrusion withoutsolid inert material. Regarding the production of disk granules,fluidized-bed granules, extruder granules and spray granules, see, forexample, the methods in “Spray-Drying Handbook” 3rd ed. 1979, G. GoodwinLtd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering1967, page 147 et seq; “Perry's Chemical Engineer's Handbook”, 5th Ed.,McGraw-Hill, New York 1973, pp. 8-57.

As regards further details on the formulation of crop protectionproducts, see, for example, G. C. Klingmam, “Weed Control as a Science”,John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer,S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell ScientificPublications, Oxford, 1968, pages 101-103.

As a rule, the agrochemical formulations comprise 0.1 to 99 percent byweight, in particular 2 to 95% by weight, of active compounds of thetypes A and/or B and/or C, the following concentrations being customary,depending on the type of formulation:

The active compound concentration in wettable powders is, for example,approximately 10 to 95% by weight, the remainder to 100% by weight beingcomposed of customary formulation constituents. In the case ofemulsifiable concentrates, the active compound concentration may amountto, for example, 5 to 80% by weight. Formulations in the form of dustscomprise, in most cases, 5 to 20% by weight of active compound,sprayable solutions approximately 0.2 to 25% by weight of activecompound. In the case of granules such as dispersible granules, theactive compound content depends partly on whether the active compound ispresent in liquid or solid form and on which granulation auxiliaries andfillers are being used. As a rule, the content amounts to between 10 and90% by weight in the case of the water-dispersible granules.

In addition, the abovementioned active compound formulations maycomprise, if appropriate, the conventional adhesives, wetters,dispersants, emulsifiers, preservatives, antifreeze agents, solvents,fillers, colorants, carriers, antifoams, evaporation inhibitors, pHregulators or viscosity regulators.

The herbicidal action of the herbicide combinations according to theinvention can be improved, for example, by surfactants, preferably bywetters from the group of the fatty alcohol polyglycol ethers. The fattyalcohol polyglycol ethers preferable contain 10-18 carbon atoms in thefatty alcohol radical and 2-20 ethylene oxide units in the polyglycolether moiety. The fatty alcohol polyglycol ethers can be nonionic orionic, for example in the form of fatty alcohol polyglycol etherssulfates, which can be used, for example, as alkali metal salts (e.g.sodium salts or potassium salts) or ammonium salts, but also as alkalineearth metal salts such as magnesium salts, such as sodium C₁₂/C₁₄-fattyalcohol diglycol ether sulfate (Genapol® LRO, Clariant); see, forexample, EP-A-0476555, EP-A-0048436, EP-A-0336151 or U.S. Pat. No.4,400,196 and also Proc. EWRS Symp. “Factors Affecting HerbicidalActivity and Selectivity”, 227-232 (1988). Nonionic fatty alcoholpolyglycol ethers are, for example, (C₁₀-C₁₈)-, preferably(C₁₀-C₁₄)-fatty alkohol polyglycol ethers containing 2-20, preferably3-15, ethylene oxide units (e.g. isotridecyl alcohol polyglycol ether),for example from the Genapol® series, such as Genapol® X-030, Genapol®X-060, Genapol® X-080 or Genapol® X-150 (all from Clariant GmbH).

The present invention furthermore embraces the combination of herbicides(A), (B) and (C) with the wetting agents mentioned above from the groupof the fatty alcohol polyglycolethers which preferably contain 10-18carbon atoms in the fatty alcohol radical and 2-20 ethylene oxide unitsin the polyglycol ether moiety and which can be present in nonionic orionic form (for example as fatty alcohol polyglycol ether sulfates).Preference is given to C12/C14-fatty alcohol diglycol ether sulfatesodium (Genapol® LRO, Clariant); and isotridecyl alcohol polyglycolether with 3-15 ethylene oxide units, for example from the Genapol® Xseries, such as Genapol® X-030, Genapol® X-060, Genapol® X-080 orGenapol® X-150 (all from Clariant GmbH). It is furthermore known thatfatty alcohol polyglycol ethers such as nonionic or ionic fatty alcoholpolyglycol ethers (for example fatty alcohol polyglycol ether sulfates)are also suitable for use as penetrants and activity enhancers for anumber of other herbicides, inter alia also for herbicides from thegroup of the imidazolinones (see, for example, EP-A-0502014).

Moreover, it is known that fatty alcohol polyglycol ethers such asnonionic or ionic fatty alcohol polyglycol ethers (for example fattyalcohol polyglycol ether sulfates) are also suitable as penetrants andsynergists for a number of other herbicides, inter alia also herbicidesfrom the group of the imidazolinones; (see, for example, EP-A-0502014).

The herbicidal effect of the herbicide combinations according to theinvention can also be increased using vegetable oils. The term vegetableoils is to be understood as meaning oils from oil-plant species, such assoya oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseedoil, coconut oil, palm oil, safflower oil or castor oil, in particularrapeseed oil, and their transesterification products, for example alkylesters, such as rapeseed oil methyl ester or rapeseed oil ethyl ester.

The vegetable oils are preferably esters of C₁₀-C₂₂-, preferablyC₁₂-C₂₀-fatty acids. The C₁₀-C₂₂-fatty acid esters are, for example,esters of unsaturated or saturated C₁₀-C₂₂-fatty acids, in particularthose with an even number of carbon atoms, for example erucic acid,lauric acid, palmitic acid and, in particular, C₁₈-fatty acids such asstearic acid, oleic acid, linoleic acid or linolenic acid.

Examples of C₁₀-C₂₂-fatty acid esters are esters obtained by reactingglycerol or glycol with the C₁₀-C₂₂-fatty acids as they exist, forexample in oils from oil-plant species, or C₁-C₂₀-alkyl-C₁₀-C₂₂-fattyacid esters as can be obtained, for example, by transesterification ofthe abovementioned glycerol- or glycol-C₁₀-C₂₂-fatty acid esters withC₁-C₂₀-alcohols (for example methanol, ethanol, propanol or butanol).Transesterification can be carried out by known methods as aredescribed, for example, in Rompp Chemie Lexikon, 9th edition, volume 2,page 1343, Thieme Verlag Stuttgart.

Preferred C₁-C₂₀-alkyl-C₁₀-C₂₂-fatty acid esters are the methyl, ethyl,propyl, butyl, 2-ethylhexyl and dodecyl esters. Preferred glycol- andglycerol-C₁₀-C₂₂-fatty acid esters are the uniform or mixed glycolesters and glycerol esters of C₁₀-C₂₂-fatty acids, in particular thosefatty acids which have an even number of carbon atoms, for exampleerucic acid, lauric acid, palmitic acid and, in particular, C₁₈-fattyacids such as stearic acid, oleic acid, linolic acid or linolenic acid.

The vegetable oils can be present in the herbicidal compositionsaccording to the invention for example in the form of commerciallyavailable oil-containing formulation additives, in particular thosebased on rapeseed oil such as Hasten® (Victorian Chemical Company,Australia, hereinbelow termed Hasten, main constituent: rapeseed oilethyl ester), Actirob®B (Novance, France, hereinbelow termed ActirobB,main constituent: rapeseed oil methyl ester), Rako-Binol® (Bayer AG,Germany, termed Rako-Binol hereinbelow, main constituent: rapeseed oil),Renol® (Stefes, Germany, termed Renol hereinbelow, vegetable oilconstituent: rapeseed oil methyl ester), or Stefes Mero® (Stefes,Germany, hereinbelow termed Mero, main constituent: rapeseed oil methylester).

In a further embodiment, the present invention embraces combinations ofherbicides (A), (B) and (C) with the vegetable oils mentioned above,such as rapeseed oil, preferably in the form of commercially availableoil-containing formulation additives, in particular those based onrapeseed oil such as Hasten® (Victorian Chemical Company, Australia,hereinbelow termed Hasten, main constituent: rapeseed oil ethyl ester),Actirob® B (Novance, France, hereinbelow termed ActirobB, mainconstituent: rapeseed oil methyl ester), Rako-Binol® (Bayer AG, Germany,termed Rako-Binol hereinbelow, main constituent: rapeseed oil), Renol®(Stefes, Germany, termed Renol hereinbelow, vegetable oil constituent:rapeseed oil methyl ester), or Stefes Mero® (Stefes, Germany,hereinbelow termed Mero, main constituent: rapeseed oil methyl ester).

For use, the formulations, which are present in commercially availableform, are optionally diluted in the customary manner, for example usingwater in the case of wettable powders, emulsifiable concentrates,dispersions and water-dispersible granules. Preparations in the form ofdusts, soil granules, granules for broadcasting and sprayable solutionsare usually not diluted further with other inert substances prior touse.

The active compounds can be applied to the plants, parts of the plants,seeds of the plants or the area under cultivation (soil of a field),preferably to the green plants and parts of the plants and, ifappropriate, additionally to the soil of the field.

One possible use is the joint application of the active compounds in theform of tank mixes, the concentrated formulations of the individualactive compounds, in optical formulations, jointly being mixed withwater in the tank and the resulting spray mixture being applied.

A joint herbicidal formulation of the combination according to theinvention of the active compounds (A), (B) and (C) has the advantage ofbeing easier to apply since the quantities of the components are alreadypresented in the correct ratio to each other. Moreover, the adjuvants inthe formulation can be matched optimally to each other.

A. General Formulation Examples

-   a) A dust is obtained by mixing 10 parts by weight of an active    compound/active compound mixture and 90 parts by weight of talc as    inert material and comminuting the mixture in a hammer mill.-   b) A wettable powder which is readily dispersible in water is    obtained by mixing 25 parts by weight of an active compound/active    compound mixture, 64 parts by weight of kaolin-containing quartz as    inert material, 10 parts by weight of potassium lignosulfonate and 1    part by weight of sodium oleoylmethyltaurinate as wetter and    dispersant, and grinding the mixture in a pinned-disk mill.-   c) A dispersion concentrate which is readily dispersible in water is    obtained by mixing 20 parts by weight of an active compound/active    compound mixture with 6 parts by weight of alkylphenol polyglycol    ether (® Triton X 207), 3 parts by weight of isotridecanol    polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral    oil (boiling range for example approx. 255 to 277° C.), and grinding    the mixture in a ball mill to a fineness of below 5 microns.-   d) An emulsifiable concentrate is obtained from 15 parts by weight    of an active compound/active compound mixture, 75 parts by weight of    cyclohexanone as solvent and 10 parts by weight of oxethylated    nonylphenol as emulsifier.-   e) Water-dispersible granules are obtained by mixing    -   75 parts by weight of an active compound/active compound        mixture,    -   10 parts by weight of calcium lignosulfonate,    -   5 parts by weight of sodium lauryl sulfate,    -   3 parts by weight of polyvinyl alcohol and    -   7 parts by weight of kaolin,    -   grinding the mixture on a pinned-disk mill and granulating the        powder in a fluidized bed by spraying on water as granulation        liquid.-   f) Water-dispersible granules are also obtained by homogenizing and    precomminuting, in a colloid mill,    -   25 parts by weight of an active compound/active compound        mixture,    -   5 parts by weight of sodium        2,2′-dinaphthylmethane-6,6′-disulfonate,    -   2 parts by weight of sodium oleoylmethyltaurinate,    -   1 part by weight of polyvinyl alcohol,    -   17 parts by weight of calcium carbonate and    -   50 parts by weight of water,    -   subsequently grinding the mixture in a bead mill and atomizing        and drying the resulting suspension in a spray tower by means of        a single-substance nozzle.-   A1. Specific formulation examples-   A1.a A water-dispersible granules (WG) formulation was prepared    containing the following active ingredients, the balance being inert    materials:    -   45 g/kg Mesosulfuron-methyl (A1-1)    -   9 g/kg Iodosulfuron-methyl-sodium (B1-2)    -   22.5 g/kg Thienecarbazone-methyl (C1-1)    -   135 g/kg Mefenpyr-diethyl (S1-1)-   A1.b An oil dispersion (OD) formulation was prepared containing the    following active ingredients, the balance being inert materials:    -   10 g/l Mesosulfuron-methyl-sodium (A1-2)    -   2 g/l Iodosulfuron-methyl-sodium (B1-2)    -   5 g/l Thienecarbazone-methyl (C1-1)    -   30 g/l Mefenpyr-diethyl (S1-1)

B. Biological Examples

Herbicidal Action (Outdoor Trials)

The seeds or rhizome pieces of typical harmful plants were planted andgrown under natural outdoor conditions. After the harmful plants hademerged, they were treated, as a rule at the 2- to 4-leaf stage, withvarious dosages of the compositions according to the invention at awater application rate of 100 to 4001/ha (converted).

After the treatment (approx. 4-6 weeks after application), theherbidical activity of the active compounds or active compound mixtureswas scored visually by comparing the treated plots with the untreatedcontrol plots. Damage and development of all above-ground parts of theplants was recorded. Scoring was done on a percentage scale (100%action=all plants dead; 50% action=50% of the plants and green plantparts dead; 0% action=no discernible action=like control plot). Thescore figures of in each case 4 plots were averaged.

The growth stages of the different weed species are indicated accordingto the BBCH monograph “Growth stages of mono- and dicotyledonousplants”, 2^(nd) edition, 2001, ed. Uwe Meier, Federal BiologicalResearch Centre for Agriculture and Forestry (Biologische Bundesanstaltfür Land and Forstwirtschaft). The respective BBCH stages are indicatedin brackets for the different weed species.

The dose rates of herbicidal ingredients used in each case are indicatedfor the respective active ingredient in brackets and refer to the amountof active ingredient per hectare (g/ha).

The following abbreviations for the active ingredient are used in theTables below:

MSM: Mesosulfuron-methyl (A1-1) or Mesosulfuron-methyl-sodium (A1-2)

IMS: Iodosulfuron-methyl (B1-1) or Iodosulfuron-methyl-sodium (B1-2)

TCM: Thienecarbazone-methyl (C1-1)

PXD: Pinoxaden

PYX: Pyroxsulam

HALXF: Halauxifen

The herbicidal effects observed for the herbicide (mixtures) areindicated in % Activity against the respective weed. The % Damageindicated refers to the maximum damage observed in the respective crop.

The results of the treatments are reflected in the Tables below, and theactivity measured for the independent use of the active compounds(A+B)+(C) is stated in brackets. The treatments were carried out usingMesosulfuron-methyl (A1-1) or Mesosulfuron-methyl-sodium (A1-2) ascomponent (A), and Iodosulfuron-methyl (B1-1) orIodosulfuron-methyl-sodium (B1-2) as component (B). The results of thetreatments in these cases were essentially identical.

TABLE 1A Combination MSM + IMS + TCM In the crop TRZDU: Triticumaestivum (durum wheat) the following weeds were treated (field trials).(MSM + IMS) TCM (MSM + IMS) + TCM Weed (15 + 3 g/ha) 7.5 g/ha (15 + 3g/ha) + 7.5 g/ha (BBCH stage) % Activity % Damage % Activity % Damage %Activity % Damage PAPRH (15) 90 0 70 0 99 (90 + 70) 0 PICEC (22) 85 2 695 92 (85 + 69) 5 AVEST (23) 63 0 33 0 100 (63 + 33) 0 LOLMU (23) 72 0 430 98 (72 + 43) 0 LOLRI (29) 80 5 52 5 100 (80 + 52) 0 Weeds treated (cf.Tables 1A and 1B) BBCH stage PAPRH: Papaver rhoeas 15: 5 true leavesPICEC: Picris echioides 22: 2 tillers visible/2 side shoots visibleAVEST: Avena sterilis 23: 3 tillers visible/3 side shoots visible LOLMU:Lolium multiflorum 23: 3 tillers visible/3 side shoots visible LOLRI:Lolium rigidum 29: 9 or more tillers visible/2 or more side shootsvisible

TABLE 1B Combination MSM + IMS + TCM In the crop TRZDU: Triticumaestivum (durum wheat) the following weeds were treated (field trials).(MSM + IMS) TCM (MSM + IMS) + TCM Weed (9 + 9 g/ha) 7.5 g/ha (9 + 9g/ha) + 7.5 g/ha (BBCH stage) % Activity % Damage % Activity % Damage %Activity % Damage PAPRH (15) 87 0 70 0 98 (87 + 70) 0 PICEC (22) 97 5 695 99 (97 + 69) 10 AVEST (23) 63 0 33 0 70 (63 + 33) 0 LOLMU (23) 65 0 430 88 (65 + 43) 0 LOLRI (29) 63 5 52 5 74 (63 + 52) 10 The same weedspecies were treated at the BBCH growth stages as in the case of TABLE1A, however here a different ratio of MSM:IMS was used.

TABLE 2A Combination MSM + IMS + TCM In the crop TRZAW: Triticumaestivum (soft wheat) the following weeds were treated (field trials).(MSM + IMS) TCM (MSM + IMS) + TCM Weed (15 + 3 g/ha) 7.5 g/ha (15 + 3g/ha) + 7.5 g/ha (BBCH stage) % Activity % Damage % Activity % Damage %Activity % Damage CENCY (19) 25 1 38 0 92 (25 + 38) 0 GALAP (23) 82 0 370 95 (82 + 37) 0 GERDI (29) 43 1 63 0 98 (43 + 63) 0 LAMAM (32) 75 10 681 99 (75 + 68) 7 LAMPU (61) 78 10 70 1 96 (78 + 70) 7 MATIN (19) 87 0 200 100 (87 + 20)  0 VERPE 72 10 10 1 90 (72 + 10) 7 VIOAR (15) 43 1 38 084 (43 + 38) 0 Weeds treated (cf. Tables 2A and 2B) BBCH stage CENCY:Centaurea Cyanus 19: 9 or more true leaves GALAP: Galium aparine 23: 3tillers visible/3 side shoots visible GERDI: Geranium dissectum 29: 9 ormore tillers visible/2 or more side shoots visible LAMAM: Lamiumamplexicaule 32: Stem (rossete) 20% of final length (diameter)/2 nodeLAMPU: Lamium purpureum 61: Beginning of flowering: 10% flowers openMATIN: Matricaria inodora 19: 9 or more true leaves VERPE: Veronicapersica VIOAR: Viola arvensis 15: 5 true leaves

TABLE 2B Combination MSM + IMS + TCM In the crop TRZAW: Triticumaestivum (soft wheat) the following weeds were treated (field trials).(MSM + IMS) TCM (MSM + IMS) + TCM Weed (9 + 9 g/ha) 7.5 g/ha (9 + 9g/ha) + 7.5 g/ha (BBCH stage) % Activity % Damage % Activity % Damage %Activity % Damage CENCY (19) 37 2 38 0 93 (37 + 38) 1 GALAP (23) 88 0 370 91 (88 + 37) 0 GERDI (29) 91 2 63 0 98 (91 + 63) 0 LAMAM (32) 88 3 681 93 (88 + 68) 13 LAMPU (61) 88 3 70 1 95 (88 + 70) 13 MATIN (19) 92 020 0 93 (92 + 20) 0 VERPE 78 3 10 1 94 (78 + 10) 13 VIOAR (15) 85 2 38 096 (85 + 38) 1 The same weed species were treated at the BBCH growthstages as in the case of TABLE 2A, however here a different ratio ofMSM:IMS was used.

TABLE 3 Combination MSM + IMS + PXD In the crop TRZAW: Triticum aestivum(soft wheat) the following weeds were treated (field trials). (MSM +IMS) PXD (MSM + IMS) + PXD Weed (15 + 3 g/ha) 60 g/ha (15 + 3 g/ha) + 60g/ha (BBCH stage) % Activity % Damage % Activity % Damage % Activity %Damage CENCY (38) 83 0 60 15 88 (83 + 60) 15 GERDI (19) 68 0 30 4 78(68 + 30) 1 VERHE (71) 45 0 13 0 68 (45 + 13) 9 VERPE (31) 33 0 0 0 53(33 + 0) 0 BROST (25) 89 0 0 0 98 (89 + 0) 0 Weeds treated (cf. Table 3)BBCH stage CENCY: Centaurea Cyanus 38: Stem (rossete) 80% of finallength (diameter)/8 node GERDI: Geranium dissectum 19: 9 or more trueleaves VERHE: Veronica hederifolia 71: 10% fruits have reached finalsize or 10% final size VERPE: Veronica persica 31: Stem (rossete) 10% offinal length (diameter)/1 node BROST: Bromus sterilis 25: 5 tillersvisible/5 side shoots visible

TABLE 4 Combination MSM + IMS + PYX (MSM + IMS) PYX (MSM + IMS) + PYXWeed (7.5 + 1.5 g/ha) 17 g/ha (7.5 + 1.5 g/ha) + 17 g/ha (BBCH stage) %Activity % Activity % Activity LOLRI (10) 35 20 73 (35 + 20)

TABLE 5 Combination MSM + IMS + HALXF In the crop TRZAW: Triticumaestivum (soft wheat) the following weeds were treated (field trials).(MSM + IMS) HALXF (MSM + IMS) + HALXF (9 + 1.8 g/ha) 276.5 g/ha (9 + 1.8g/ha) + 276.5 g/ha Weed % Activity % Damage % Activity % Damage %Activity % Damage CENCY 40 0 45 0 85 (40 + 45) 5 FUMOF 93 0 85 0 99(93 + 85) 5 GALAP 88 0 73 0 98 (88 + 73) 5 PAPRH 83 0 75 0 95 (83 + 75)5 Weeds treated (cf. Table 5): CENCY: Centaurea Cyanus FUMOF: Fumariaofficinalis GALAP: Gallium aparine PAPRH: Papaver rhoeas

The invention claimed is:
 1. An herbicide composition comprising an effective amount of components (A), (B) and (C), wherein (A) denotes mesosulfuron-methyl (A1-1) and/or mesosulfuron-methyl sodium (A1-2); (B) denotes iodosulfuron-methyl (B1-1) and/or iodosulfuron-methyl sodium (B1-2); (C) denotes (C-2) pyroxsulam or a salt thereof; wherein the weight ratio of the components A and B to one another is 5:1 to 1:1, wherein the weight ratio of the two components (A+B) and C to each other is 1:1 to 1:3, and wherein (A), (B), and (C) are the only herbicides in the composition.
 2. The herbicide composition as claimed in claim 1 which additionally comprises one or more further components selected from the group consisting of agrochemically active compounds of a different type, formulation auxiliaries and additives customary in crop protection.
 3. The herbicide-composition as claimed in claim 1 which additionally comprises one or more safeners.
 4. The herbicide composition as claimed in claim 3, wherein the safener is, mefenpyr-diethyl (S1-1).
 5. The herbicide composition as claimed in claim 1, which additionally comprises one or more fatty alcohol polyglycol ethers and/or one or more vegetable oils.
 6. The herbicidal composition according to claim 1, wherein components (A), (B), and (C) are present in synergistically effective amounts.
 7. The herbicidal composition as claimed in claim 1, wherein the weight ratio of the two components (A+B) and C to each other is 1:1 to 1:2.
 8. The herbicide composition according to claim 1, wherein the weight ratio of the two components (A+B) and C to each other is 1:1.9 to 1:3.
 9. A method for controlling undesired plant growth which comprises applying herbicides (A), (B) and (C) onto a plant, a part of plants, one or more plant seeds and/or an area where plants grow, wherein (A) denotes mesosulfuron-methyl (A1-1) and/or mesosulfuron-methyl sodium (A1-2), (B) denotes iodosulfuron-methyl (B1-1) and/or iodosulfuron-methyl sodium (B1-2), (C) denotes (C-2) pyroxsulam or a salt thereof, wherein the weight ratio of the components A and B to one another is 5:1 to 1:1, wherein the weight ratio of the two components (A+B) and C to each other is 1:1 to 1:3, and wherein (A), (B), and (C) are the only herbicides in the composition.
 10. The method as claimed in claim 9 comprising the selective control of one or more harmful plants in one or more plant crops.
 11. The method as claimed in claim 10 comprising the control of harmful plants in crops of monocotyledonous plants.
 12. The method as claimed in claim 10 in which the plant crops are genetically modified or have been obtained by mutation/selection.
 13. The method according to claim 9, wherein the herbicides (A), (B), and (C) are applied together.
 14. The method according to claim 9, wherein the weight ratio of the two components (A+B) and C to each other is 1:1 to 1:2.
 15. The method according to claim 9, wherein the weight ratio of the two components (A+B) and C to each other is 1:1.9 to 1:3. 